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Synthesis 2023; 55(18): 2833-2842
DOI: 10.1055/a-2020-8923
DOI: 10.1055/a-2020-8923
short review
Special Issue Electrochemical Organic Synthesis
Recent Advances in Electro- or Photochemical Driven Transformations via Cleavage of the C–N Bond of Quaternary Ammonium Salts
We thank the funding from the National Natural Science Foundation of China (NSFC) (22102012, 22202021, 22272011, and 22201062), Changzhou Science and Technology Plan Applied Basic Research Project (CJ20210159, CJ20210129, and CZ20220022), Natural Science Foundation of Henan Province (K22029Y), the Jiangsu Higher Education Institutions of China (22KJA150001, 21KJD530003, 21KJB530013), and the opening funding of Hubei Key Laboratory of Natural Products Research and Development, China Three Gorges University (2022NPRD02).
Abstract
Selective functionalization via cleavage of the C–N bond of amines has proven to be challenging partly because of its relatively high bond dissociation energy, even though amines are abundant and readily available. To meet this challenge, many new transformations based on the pre-activation of the C–N bond before the cleavage have been developed. Among them, the conversion of amines into quaternary ammonium salts has certain advantages, such as easy preparation from primary, secondary, or tertiary amines, as well as stable storage and usage. Although transition metal catalysis has been frequently applied for developing new transformations via oxidative addition of the C–N bond of quaternary ammonium salts, recent studies have shown a new dimension by using green electro- or photochemical tools. In this short review, recent advances in electro-, photo-, or photoelectrochemical driven synthetic applications of quaternary ammonium salts have been summarized and discussed.
1 Introduction
2 Electrochemical Driven Transformations
3 Photochemical Driven Transformations
4 Photoelectrochemical Driven Transformations
5 Conclusion and Outlook
Key words
quaternary ammonium salts - synthetic transformation - C–N bond cleavage - amines - electrochemistry - photochemistryPublication History
Received: 30 December 2022
Accepted after revision: 26 January 2023
Accepted Manuscript online:
26 January 2023
Article published online:
01 March 2023
© 2023. Thieme. All rights reserved
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For selected reviews, see:
For other recent cyanations, see:
See also:
See also:
For a recent example to form benzylic radical, see:
For recent selected reviews, see:
For recent selected examples, see: